Trifluoroacetic acid → HCID 59616623, compound

Participants

Reaction Steps

A solution of the product from Example 189A (30 mg, 0.036 mmol) in a 1:1 mixture of CH2Cl2:TFA (0.4 mL) was stirred at rt for 45 min. The mixture was concentrated in vacuo, and the residue was partitioned between saturated aq. NaHCO3 and EtOAc (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a solid. The solid was subjected to the procedure described in Example 189A (27 mg), substituting (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid for (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid, to give the title compound (17 mg, 52%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.85-0.97 (m, 6H), 1.08-1.19 (m, 12H), 1.60-1.66 (m, 2H), 1.80-2.05 (m, 8H), 2.08-2.20 (m, 2H), 3.25 (s, 3H), 3.42-3.50 (m, 2H), 3.52 (s, 3H), 3.53 (s, 3H), 3.58-3.72 (m, 2H), 3.76-3.87 (m, 2H), 3.98-4.06 (m, 1H), 4.26 (t, J=7.81 Hz, 1H), 4.38-4.46 (m, 2H), 5.15 (d, J=6.40 Hz, 2H), 6.17 (d, J=8.78 Hz, 2H), 6.94 (d, J=8.89 Hz, 2H), 7.13 (d, J=8.24 Hz, 4H), 7.32 (t, J=8.84 Hz, 2H), 7.49 (dd, J=8.57, 2.06 Hz, 4H), 9.96 (d, J=15.51 Hz, 2H). MS (ESI) m/z 910.6 (M+H)+.

Provenance & Evidence